Hydrochloric Acid → HCID 13787428, compound

HRID 1165225Notes

Reaction equation

HRID 1165225 reaction equation
C([Al](CC(C)C)CC(C)C)C(C)C.[NH2:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2.[C:24](OC)(=[O:32])[C:25]1[C:26](=[CH:28][CH:29]=[CH:30][CH:31]=1)[OH:27].Cl>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl.C(Cl)Cl>[OH:27][C:26]1[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=1[C:24]([NH:14][C:15]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:16]=1[CH:17]=[CH:18][NH:19]2)=[O:32]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 4133Methyl SalicylateHCID 5834314-AminoindoleHCID 16682931Triisobutylaluminum

Product 1

HCID 13787428HCID 13787428, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

92 ml of a solution of 1.1 mol/l of triisobutylaluminum in toluene were added slowly with stirring under an inert atmosphere to a solution of 6.6 g of 4-aminoindole in 250 ml of chloroform. 9.6 ml of methyl salicylate were then added and the mixture was refluxed for 20 hours and then cooled to room temperature. 300 ml of N hydrochloric acid and 300 ml of methylene chloride were added and the organic phase was washed with water, dried, and evaporated to dryness under reduced pressure at 50° C. The residue was made into a paste with ether, filtered and dried at 60° C. under reduced pressure to obtain 9.4 g of 2-hydroxy-N-(1H-indol-4-yl)benzamide melting at ≃232° C.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. washthe organic phase was washed with water
  3. customdried
  4. customevaporated to dryness under reduced pressure at 50° C
  5. filtrationfiltered
  6. customdried at 60° C. under reduced pressure

Sources & evidence

ORD record
ord-301cbdbc28a84e3aa30d8c1580b4f67a
Source dataset
uspto-grants-1990_03
Patent number
US04908367

Reaction notes

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